Trifluoroacetic acid → Methyl 6-iodo-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate
Reaction equation
[CH3:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:4](=[O:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.FC(F)(F)C(O)=O.[I:30]N1C(=O)CCC1=O.[Al]>O.C(Cl)Cl>[I:30][C:7]1[N:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[C:4](=[O:12])[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)[C:2]=1[CH3:1]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl 5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (described in the synthesis of SM2, 1.5 g, 4.8 mmol), dry DCM (7.0 mL), trifluoroacetic acid (3.0 mL) and N-iodosuccinimide (1.0 g, 4.5 mmol) were mixed and stirred at RT in the dark (flask covered with aluminum foil). After 5 h, water (5 mL) was added and the mixture was concentrated by rotary evaporation. Water (3 mL) was added once more and the mixture was concentrated as described above. The resulting mixture was diluted with acetonitrile to a total volume of 50 mL. Purification by preparative HPLC with acetonitrile-water as eluent (neutral eluent) gave 0.905 g (46% yield) of the title compound as a yellow crystalline solid.
Workup
- additionwere mixed
- concentrationthe mixture was concentrated by rotary evaporation
- additionWater (3 mL) was added once more
- concentrationthe mixture was concentrated
- additionThe resulting mixture was diluted with acetonitrile to a total volume of 50 mL
- customPurification by preparative HPLC with acetonitrile-water as eluent (neutral eluent)
Sources & evidence
- ORD record
- ord-0552440ecc5247378cb8dbaca0e5397a
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08114881B2
Reaction notes
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